


Office Dealings

by Angelicfall67



Category: Supernatural
Genre: Age Swap, Blindfolds, Crying Dean, Dom Sam, Dubious Consent, Gags, M/M, Not Brothers AU, Office AU, Orgasm Denial, Rape/Non-con Elements, Sex Toys, Size Kink, Sub Dean, dubcon
Language: English
Status: Completed
Published: 2016-12-18
Updated: 2016-12-18
Packaged: 2018-09-09 12:25:49
Rating: Explicit
Warnings: Rape/Non-Con
Chapters: 1
Words: 1,999
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8890696
Author URL: https://archiveofourown.org/users/Angelicfall67/pseuds/Angelicfall67
Summary: After all, Dean was his good boy.





	

**Author's Note:**

  * For [samalambis](https://archiveofourown.org/users/samalambis/gifts).



There was nothing that Sam Wesson couldn’t afford. 

 

At just thirty-five years old, he owned the most profitable company in the country, and had buildings all over the country. His work ethic was called ‘ruthless’ by others. Any company he deemed as a threat was bought out by him. Any that didn’t comply to his demands? Well, they would, in time, go down. Whether because of their customers suddenly pulling away, or due to a huge scandal. 

 

Straightening his tie, Sam headed to his office. He owned many things, but the best possession he had? A pretty, twenty-three year old that had a sweet mouth, and a nice little body. Dean Winchester was, or rather, had been, a simple paper pusher. Someone on the lower levels of his company that Sam wouldn’t have noticed had Dean not accidentally ran into him one morning. Immediately Sam had been drawn in by those pretty green eyes, that lithe body and the way Dean stammered out an apology. Those lips, God, those lips. 

 

Sam had to have him. 

 

So, he’d called him to his office that same day. He’d been blunt in his demands, and Dean, pretty, shy, little Dean had stammered and stuttered, declining his gracious offer. It had been painfully obvious that Dean was stressed that day, so Sam had dismissed him before starting to research the boy. 

 

Dean Winchester was only twenty-three. He had a ton of debts from college, and his father was a deadbeat who had gambling debts that he was trying to work to pay off on top of his own debt. He lived in a shabby little apartment, barely getting by on his own. Sam couldn’t leave his poor baby to suffer, could he? 

 

So, he’d called Dean to his office the next day. The contract he’d laid out was simple. Sam would pay off every debt he owed, even his father’s gambling debts, and Dean just had to become Sam’s. That mean he would do anything that Sam wanted. His life belonged to him if he agreed. Dean’s pretty eyes grew wide as he read over the paper, and he had signed his life away, although reluctantly. 

 

The first thing Sam had done was drag his boy into his lap and kiss him senseless. Dean was so small that he easily fit in his lap. Sam couldn’t wait to see what he’d look like riding him. When he’d found out Dean was a virgin? That had been even better. 

 

That night, Sam had been gentle. He’d gone slow, taking his time opening Dean up, first with his tongue and then his fingers. Watching his cock sink into that pretty little hole had been amazing. Dean had cried, said it was too big, that he wouldn’t fit, but Sam just pulled Dean into his lap, impaling him onto his cock. Dean had cried so pretty, and Sam swore he could feel his cock when he pressed his hand on that little tummy. 

 

Opening the door to his office, Sam smiled when he heard the sound of little whimpers. Ever since that night, he always made sure his little boy was ready for him. Dean had snapped at him last night, called him a bastard and Sam didn’t tolerate disrespect. Going over to his desk, Sam looked underneath it. 

 

Dean was so small that he fit under there so perfectly, and he looked so pretty right now. A sybian may be a machine meant for women, but it was working perfectly right now. Dean was tied down onto it, hands bound behind his back, a thick toy the size of Sam’s own cock filling him up. The machine was left on high last night, and a pretty little cock ring had kept Dean’s orgasm at bay. A blindfold took away his sight, ear plugs had blocked out all sound, and a nice ring gag held that pretty mouth open in a wide O. Nipple clamps were pinching those sensitive nipples, the chain pulled down and attached to the cock ring. 

 

There were tears running down freckled cheeks, drool constantly sliding down Dean’s chin. He looked like a beautiful, fucked out mess. Sam sat down at his desk and guided his erection through the gag, groaning at the way Dean’s throat constricted whenever he went too far. Well, now was a good time as any to work on the boy’s gag reflex. He kept on hand on the back of Dean’s head, holding him down onto his cock, absently petting his hair while he got to work. 

 

Sam sat there a few hours, just holding Dean like that. Eventually, he started fucking brutally into that mouth, teaching his boy a lesson. Sam would make sure that Dean couldn’t talk by the end of today. He would not tolerate disrespect from his boy. When he felt close, he shoved all the way down and came, too far down for Dean to do anything else but swallow his load. When he finally pulled out, Dean’s lips looked swollen and red. The sounds he made were absolutely heart breaking. But Sam had to teach him a lesson. 

 

Carefully removing the ear plugs, Sam gently tapped on Dean’s cheek. “Baby,” His voice was gentle, despite the torment he’d left Dean to face all night. Dean’s response was a high pitched whine. “Listen to me, Baby. Nod if you understand.” It took a second, but his boy finally gave a weak nod. “Good boy. Now, I’m going to take you off of this machine, alright?” Another nod, and a whimper. “You’re going to behave for me, take everything I give you today, right? If you’re a good boy, I’ll let you come and bring you home.” A more frantic nod, and a desperate little noise. 

 

Satisfied that his boy would listen, Sam carefully untied Dean’s legs and turned off the sybian. Gentle, he picked his boy up and sat him in his lap. Since he hadn’t untied Dean’s arms, his boy was trying to get closer to him, making helpless little noises. Sam knew Dean could be so sweet when he just listened. Gently laying Dean on his desk on his stomach, Sam spread his legs. His little hole was red and puffy, but otherwise fine. Pushing his fingers inside, he was rewarded with a high whine from the boy. It seems the night on the sybian had made Dean all the more sensitive. Good. 

 

Spreading those legs wider, Sam finally took notice of his boy’s cock. It was red and angry looking, leaking from the tip from his prolonged denial. Ever since this arrangement started, Sam never once touched Dean’s cock. He would learn to come on Sam’s cock alone and nothing else. It’s been two months and Dean still hadn’t learned how just yet. Sometimes, when he was especially good, Sam would hold a vibrator to his cock and let Dean come. Most of the time? Dean would get off on Sam pounding his prostate or being milked. 

 

“My poor boy,” Sam cooed softly, tugging Dean into his lap. This time, he set Dean onto his cock, smiling at the noise Dean made when he was impaled once more. God, it felt so good, hot and tight. Just for fun, he tugged on the nipple clamps, further tormenting those abused buds and earning himself a sob from his boy. The day wasn’t over yet. 

 

Smacking his ass, he ordered Dean to sit still and let the boy rest his head against his chest. Dean finally settled down and Sam gently ran his hand through his hair. “Good boy. Now, just stay right there while I work.” 

 

The hours passed by and Sam could see Dean was trying to behave. However, Sam had purposely adjusted Dean so that his cock was constantly rubbing on Dean’s prostate. It only took a few hours before Dean was sobbing again, trying to beg around the gag. Sam studiously ignored him, although he wrapped an arm around his waist to keep him still. When the last paper was signed, he decided it was enough. 

 

Gripping those slim hips, Sam pulled Dean up until just the head of his cock was inside of him. Then, he slammed him back down, repeating this over and over until his boy was a complete mess. An idea came to him. Carefully, Sam took off the cock ring from Dean and started fucking him harder. Dean squirmed and writhed, reacting beautifully but his cock stayed hard.

 

Maybe it was cruel to avoid his prostate, but Dean was still being punished. Sam didn’t let up, however, drawing this out for a while before finally releasing inside of his boy. When he was done, he tugged Dean back onto his lap, impaling him once more. 

 

Carefully, Sam removed the gag and massaged Dean’s sore jaw. “Got anything to say?” He asked, ignoring the impulse to just coddle his boy already. 

 

Dean sucked in a breath, and when he spoke, his voice sounded well fucked. “Sorry, I’m sorry, I’m sorry, please, I’m sorry!” The apologies tumbled out, and he hiccuped and sobbed. After a few moments, Sam was satisfied that his boy had learned his lesson. Gentle, he turned Dean around in his lap and took off the blindfold, looking into teary green eyes. 

 

“Good boy,” Sam praised gently, tugging Dean into a gentle kiss. His boy responded beautifully, kissing him back desperately, tugging at his restraints in an adorable effort to get free so he could hold on to Sam. 

 

“Shh. You’re such a good boy, Dean,” Sam cooed, gathering his boy into his arms and hugging him close. A smile tugged at his lips when Dean snuggled into his chest. “Now, I’m not done with you yet. Let’s see how good of a boy you can be.” Without giving his boy a chance to question what he meant, Sam gripped those hips and once more started using Dean’s body. Only this time, he aimed right for his prostate at every thrust, punching out moans and whimpers from his boy. He tugged at the clamps, and Dean started crying again. Only this time, finally, when Sam came, so did Dean. All without having his cock touched. 

 

The punishment was over. Dean had done so well in taking it that Sam couldn’t stand it any longer. He removed the restraints, took off the clamps even as Dean cried, and tugged his boy into his lap, cooing praises to him. 

 

The rest of the day was spent like that. Dean in his lap, sitting on his cock, legs on either side of Sam and clutching desperately to him. Sam stroked his back, pet his hair until his boy was finally calm, although he took pleasure in playing with those sore little nipples or occasionally nudging his cock against his boy’s prostate. Each time, Dean would whine or whimper but he never protested against it. When it was time to go home, Dean was once again erect but Sam ignored his boys needs for now. 

 

Pulling his boy off, Sam stood up and started packing his things. He noticed the scared look on Dean’s face and another smile tugged at his lips. His boy thought he was going to leave him here again? That was good. Ignoring Dean a little longer, he finally heard a whimper from him. Going over to Dean, Sam gently wrapped him up in his jacket, the material swallowing Dean up. Then, he scooped him into his arms and kissed him gently while carrying him out of the office. Despite the building being empty, Dean still clung to Sam and his face still turned red in embarrassment. 

 

As he got into his car, tugging Dean into his lap once more and petting his boy’s hair, Dean finally cuddled close to his chest. It had been an especially hard day on his boy, but Sam was positive that Dean wouldn’t disrespect him again anytime soon. 

 

After all, Dean was his good boy.


End file.
